N-Acetyltyramine

Names

[ Name ]:
N-Acetyltyramine

[Synonym ]:
GNF-PF-5230
N-Acetyltyramine
N-acetyltyramin
N-[2-(4-Hydroxyphenyl)ethyl]acetamide
Acetamide, N-[2-(4-hydroxyphenyl)ethyl]-

Biological Activity

[Description]:

N-Acetyltyramine is a quorum-sensing inhibitor (QSI) compound produced by V. alginolyticus M3-10. N-Acetyltyramine is capable of inhibiting the QS of C. violaceum ATCC 12472. N-acetyltyramine reverses resistance in Doxorubicin-resistant leukemia P388 cells[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

N-Acetyltyramine enhances cytotoxicity of doxorubicin in resistant P388 murine leukemia cells with an IC50 value of 0.13 μg/ml compared with an IC50 value of 0.48 µg/ml for doxorubicin alone[2].

[References]

[1]. Reina JC, et al. A Quorum-Sensing Inhibitor Strain of Vibrio alginolyticus Blocks Qs-Controlled Phenotypes in Chromobacterium violaceum and Pseudomonas aeruginosa. Mar Drugs. 2019;17(9):494. Published 2019 Aug 24.

[2]. Kunimoto S, et al. Reversal of resistance by N-acetyltyramine or N-acetyl-2-phenylethylamine in doxorubicin-resistant leukemia P388 cells. J Antibiot (Tokyo). 1987;40(11):1651-1652.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
424.1±28.0 °C at 760 mmHg

[ Melting Point ]:
134°C

[ Molecular Formula ]:
C₁₀H₁₃NO₂

[ Molecular Weight ]:
179.216

[ Flash Point ]:
210.3±24.0 °C

[ Exact Mass ]:
179.094635

[ PSA ]:
49.33000

[ LogP ]:
0.39

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.546

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC3852300

CHEMICAL NAME :: Acetamide, N-(2-(4-hydroxyphenyl)ethyl)-

CAS REGISTRY NUMBER :: 1202-66-0

BEILSTEIN REFERENCE NO. :: 2096467

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H13-N-O2

MOLECULAR WEIGHT :: 179.24

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Cardiac - cardiomyopathy including infarction Skin and Appendages - hair

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 38,474,1976

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H318

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Selective nanomolar detection of dopamine using a boron-doped diamond electrode modified with an electropolymerized sulfobutylether-beta-cyclodextrin-doped poly(N-acetyltyramine) and polypyrrole composite film.

Anal. Chem. 81(10) , 4089-98, (2009)

N-acetyltyramine was synthesized and electropolymerized together with a negatively charged sulfobutylether-beta-cyclodextrin on a boron-doped diamond (BDD) electrode followed by the electropolymerizat...

Mechanistic and structural analysis of Drosophila melanogaster arylalkylamine N-acetyltransferases.

Biochemistry 53(49) , 7777-93, (2014)

Arylalkylamine N-acetyltransferase (AANAT) catalyzes the penultimate step in the biosynthesis of melatonin and other N-acetylarylalkylamides from the corresponding arylalkylamine and acetyl-CoA. The N...

Effect of acetyl derivatives of some sympathomimetic amines on the blood pressure of the rat.

Acta Pharmacol. Toxicol. (Copenh.) 40(2) , 247-58, (1977)

The effect of five sympathomimetic amines and some of their acetyl derivatives on the blood pressure of the rat was determined on the left carotid artery. After pretreatment with chlorisondamine (1 mg...

Related Compounds

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